Details of the Drug

General Information of Drug (ID: DMZO10Y)

Drug Name
Testosterone undecanoate
Synonyms Restandol (TN)
Indication
Disease Entry ICD 11 Status REF
Hypogonadism 5A61.0 Approved [1]
Affected Organisms
Humans and other mammals
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 456.7
Logarithm of the Partition Coefficient (xlogp) 8.5
Rotatable Bond Count (rotbonds) 11
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Elimination
90% of an intramuscularly administered dose of testosterone is conjugated and eliminated in the urine, and approximately 6% of the dose is eliminated primarily unconjugated in the feces []
Half-life
The concentration or amount of drug in body reduced by one-half in 33.9 days [2]
Metabolism
The drug is metabolized via the non specific esterases [3]
Chemical Identifiers
Formula
C30H48O3
IUPAC Name
[(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] undecanoate
Canonical SMILES
CCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
InChI
InChI=1S/C30H48O3/c1-4-5-6-7-8-9-10-11-12-28(32)33-27-16-15-25-24-14-13-22-21-23(31)17-19-29(22,2)26(24)18-20-30(25,27)3/h21,24-27H,4-20H2,1-3H3/t24-,25-,26-,27-,29-,30-/m0/s1
InChIKey
UDSFVOAUHKGBEK-CNQKSJKFSA-N
Cross-matching ID
PubChem CID
65157
ChEBI ID
CHEBI:135741
CAS Number
5949-44-0
UNII
H16A5VCT9C
DrugBank ID
DB13946
TTD ID
D02AXG
INTEDE ID
DR1566
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [4]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [5]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [6]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [7]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [8]
Cytochrome P450 3A7 (CYP3A7) DERD86B CP3A7_HUMAN Substrate [9]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
15-hydroxyprostaglandin dehydrogenase (HPGD) OTYZI6JB PGDH_HUMAN Gene/Protein Processing [10]
ADP-ribosylation factor-like protein 9 (ARL9) OTCP868V ARL9_HUMAN Gene/Protein Processing [10]
Alpha-protein kinase 2 (ALPK2) OTWZZDQ9 ALPK2_HUMAN Gene/Protein Processing [10]
AMP deaminase 3 (AMPD3) OT5SP1KJ AMPD3_HUMAN Gene/Protein Processing [10]
Apoptosis facilitator Bcl-2-like protein 14 (BCL2L14) OT87E7HW B2L14_HUMAN Gene/Protein Processing [10]
Atrial natriuretic peptide-converting enzyme (CORIN) OT4SK7DK CORIN_HUMAN Gene/Protein Processing [10]
C-C motif chemokine 18 (CCL18) OT7JYSK9 CCL18_HUMAN Gene/Protein Processing [10]
C-X-C motif chemokine 10 (CXCL10) OTTLQ6S0 CXL10_HUMAN Gene/Protein Processing [10]
Calcineurin B homologous protein 2 (CHP2) OT4UMKUR CHP2_HUMAN Gene/Protein Processing [10]
CCN family member 3 (CCN3) OTOW5YL4 CCN3_HUMAN Gene/Protein Processing [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Intramuscular injection of testosterone undecanoate for the treatment of male hypogonadism: phase I studies. Eur J Endocrinol. 1999 May;140(5):414-9.
3 Bruce RB, Turnbull LB, Newman JH: Metabolism of methocarbamol in the rat, dog, and human. J Pharm Sci. 1971 Jan;60(1):104-6.
4 Human cytochrome p450 induction and inhibition potential of clevidipine and its primary metabolite h152/81. Drug Metab Dispos. 2006 May;34(5):734-7.
5 Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9.
6 In vitro metabolism of midazolam, triazolam, nifedipine, and testosterone by human liver microsomes and recombinant cytochromes p450: role of cyp3a4 and cyp3a5. Drug Metab Dispos. 2003 Jul;31(7):938-44.
7 Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425.
8 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
9 Steroid hydroxylation by human fetal CYP3A7 and human NADPH-cytochrome P450 reductase coexpressed in insect cells using baculovirus. Res Commun Mol Pathol Pharmacol. 1998 Apr;100(1):15-28.
10 Levonorgestrel enhances spermatogenesis suppression by testosterone with greater alteration in testicular gene expression in men. Biol Reprod. 2009 Mar;80(3):484-92.